


You really tried your hardest

by Lolly_XX



Series: Daddy Sam [2]
Category: Supernatural
Genre: Cumming For The First Time, Hand Jobs, M/M, Omorashi, Pants wetting, Sam Winchester is Daddy, Uncle Gabriel (Supernatural), showering together
Language: English
Status: Completed
Published: 2020-10-08
Updated: 2020-10-08
Packaged: 2021-03-08 02:08:29
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 1,226
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26897953
Author URL: https://archiveofourown.org/users/Lolly_XX/pseuds/Lolly_XX
Summary: Jack and Sam have some unplanned fun.
Relationships: Jack Kline & Sam Winchester
Series: Daddy Sam [2]
Series URL: https://archiveofourown.org/series/1962523
Kudos: 39





	You really tried your hardest

**Author's Note:**

> I keep tagging underage because it depends on your interpretation of Jack. I'm writing him as 19 in this series, but I didn't want there to be any possible issues :)

A few weeks later, and after several more intentional wettings, Jack was left alone with Sam when Dean and Castiel went on a hunt together. Jack hadn't really intended on getting as desperate as he was, it kind of happened by accident. He had been trying to see how long he could hold his bladder for in the last week, and forgot he wasn't alone with the other men to distract each other from his antics. 

But here he was, sitting in the old leather chair across from Sam with his legs curled under him, his bladder growing fuller and fuller with each passing minute. He was sipping the tea Sam had made them and flipping through a book. Sam was in the chair across from him reading. That's all they did these days, reading and studying how to best defeat the next monster. 

After 15 minutes passed Jack started to get all wiggly. This was by far the longest he had ever held without relieving himself. Sam glanced up every once in a while when he heard the squeak of the cushion. It thrilled Jack that he might get caught by none other than Sam. 

Another 20 minutes went by and Jack was really on the verge of losing it. He wanted nothing more than to just sit there and wet his pants in front of Sam, to have him comfort Jack even if he didn't really need it. 

But he started to get nervous and have some reservations. He didn’t really have time for second thoughts, though, because when he stood up he felt all the pressure shift in his bladder, now pressing down, desperate to come out. He sucked in air through his teeth, causing a loud hissing sound that alarmed Sam. 

“Jack! Are you okay?” he went to Jack who was now doubled over, hands shoved between his thighs. 

“Sam,” Jack whined, looking up through the tops of his lids. “I… I…” He suddenly felt embarrassed, heat prickled at the tips of his ears. 

Sam had kind of guessed what was going on from all the squirming, but he wasn’t sure if Jack was doing it on purpose or if it truly was a miscalculation. And wouldn’t it be inappropriate for Sam to buy into it? Even if Jack was 19 the age gap alone was jarring. But God, did Sam eat this up. 

“It’s okay, Jack,” Sam decided to play along. “You really tried your hardest.” 

Jack smiled at Sam briefly before another wave of desperation hit him. 

“Oh. Oh no,” he tried to sound like the people he saw in the videos. “I think I’m having an accident. Sam?” 

Jack’s eyes were pleading. Sam pulled Jack to his chest and stroked his hair. 

“It’s okay, shhh.” Jack nuzzled in, finally relaxing his body and removing his hands from his crotch. 

It was a feeling like no other. Sure, he’d been wetting himself for a few weeks now, but not like this. Not this desperate, not being held by Sam. He thrust his hips forward making sure the front of his pants would press against him the way he liked. When it was all over -- sooner than they both would have liked -- they surveyed the damage. 

“Was that good?” Jack panted into Sam’s shirt. 

Sam smiled down at Jack. “Yeah, Jack. You’re a good boy.” 

Jack practically purred as Sam collected him up off the floor and started for the showers. 

“But the mess?” Jack looked over Sam’s shoulder at the large puddle on the floor. 

“I’ll get it later, don’t worry about it.” 

In the shower Sam lowered Jack onto the smooth floor and turned to leave. 

“Wait,” Jack said in a very small voice. “Will you stay?” 

Sam couldn’t resist the look on Jack’s face. “Is that what you want?” 

“Yes.” Jack said, very surely. 

Sam joined him in one of the larger stalls and helped Jack disrobe. Jack gasped when Sam was unzipping his pants, his body responded to the touch of Sam’s hand. 

When Jack was naked standing in the cascading water he blinked at Sam. “Aren’t you joining?” 

“I, uh, I can if you want.”

“Please!” Jack was a little too eager. 

Sam took his own clothes off, tossing them to the side and stepped in. Jack couldn’t stop looking at Sam, all this time he imagined what his body might look like based on people on the internet. It was firm but also soft in a really comforting way, but what he really fixated on was between Sam’s legs. It wasn’t that much larger than his own penis, but the size was still noticeably different. 

“Can I… touch it?” 

Sam chuckled, “uhm, sure.” 

Jack reached out a slender finger and poked at Sam’s hardness. Sam smiled, a confused look flashing across his face. But then Jack ran his finger along its length, it made Sam shiver so Jack decided to wrap a hand around it, like he does his own when he uses the toilet. Sam seemed to like it when Jack moved his hand up and down the shaft so he kept on doing that. Soon Sam was panting and moaning and closing his eyes and then his whole body went rigid. Jack felt a movement in his hand and watched as some white sticky liquid leaked out. He quickly moved his hand away and looked up at Sam’s face. He didn’t appear to be injured. 

“Sam? Are you okay? I’m sorry I didn’t know…” 

Sam scrunched up his face. “Jack, what do you -- Have you never touched yourself before?” 

“I… didn’t know I was supposed to.” 

Again, Sam let out a chuckle. “Well, you don’t have to. But people’s bodies were made to feel good from touching certain areas.” 

“Oh…” Jack thought for a moment. “If you don’t touch it, does your body get angry?” 

“Well, I guess if you get yourself worked up without any release, it might seem that way.” 

Jack looked at his own body now, his penis was reddish, pointing straight up at him, his balls were pulled up tight to his body. He slid a hand down and gripped himself. The sensation was surreal and he felt dizzy with urgency. He tightened his hand and started pumping his fist as fast as he could before feeling Sam’s hand pulling his own away. He wanted to cry from the loss of his own hand but then Sam replaced it. His hand was large and warm and gentle. He moved it slowly at first, picking up speed until Jack was involuntarily bucking his hips to match the rhythm. 

When he came he saw stars and it was like his whole body was drowning in good. 

“Wow,” Jack said, breathlessly. “I didn’t know I could do that.” 

Sam smiled lovingly at Jack and drew him in for a hug. They washed each other quickly and left the shower to return to the real world. Sam tucked Jack into bed and left to take care of the mess from earlier. He was slightly horrified to return to the scene only to find no remnants of their earlier happenings. 

He did find a note with a familiar scrawl. 

‘Took care of your little naughty mess. Glad you found someone to share your dirty little secret with, ya freak. With all my love.’   
-G

**Author's Note:**

> Is Gabriel a Voyeur? I believe he would be. Also, he's still alive because I love him, okay?
> 
> How many times has Gabriel looked in on the boys to find them doing something shameful or kinky? The world may never know.


End file.
